CN109054439B - Phthalocyanine azo-based double-chromophore bright green reactive dye and preparation method and application thereof - Google Patents
Phthalocyanine azo-based double-chromophore bright green reactive dye and preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/10—Porphines; Azaporphines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0003—Drying, e.g. sprax drying; Sublimation of the solvent
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
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Abstract
The invention relates to a phthalocyanine azo-based double-chromophore bright green reactive dye and a preparation method and application thereof. The dye obtained by the invention is suitable for printing cotton, linen and other textiles, solves the problems of color matching compatibility of two dyes in the practical application process and the like, and the printed fabric shows good light color fastness and medium printing color fixing rate, thereby having good application prospect.
Description
Technical Field
The invention belongs to the field of reactive dyes, and particularly relates to a light green reactive dye based on phthalocyanine azo-based double-color body, and a preparation method and application thereof.
Background
The reactive dye can be combined with fiber by covalent bond, has excellent wet treatment fastness and level dyeing performance, bright color, complete color spectrum and low cost, and is developed rapidly. In the reactive dye, light color varieties such as yellow, orange, red and the like are mostly azo structures, purple, brown and black varieties are commonly in metal complex azo structures, and brilliant blue is mostly anthraquinone derivatives. The reactive turquoise blue dye with the parent body of copper phthalocyanine always occupies a very important position due to the unique turquoise blue color and luster, and is an indispensable reactive dye for dyeing bright green color and luster and color matching of cellulose fiber. At present, the reactive turquoise blue dye is commonly used for blending the bright green and brilliant green with the reactive bright yellow dye, and the problems of poor color reproducibility, large vat error, influence on color fastness and the like of a printed fabric can occur due to different dye structures and different dye uptake rate, lifting power, fixation rate and the like of each dye in the green blending process, so that the development of the bright green reactive dye with a single structure has very important significance for improving the color blending reproducibility.
Disclosure of Invention
The invention provides a phthalocyanine azo-based double-chromophore bright green reactive dye and a preparation method and application thereof, and solves the problems of the compatibility of the phthalocyanine-based reactive turquoise blue dye and the reactive bright yellow dye in practical application.
The invention provides a phthalocyanine azo-based double-chromophore bright green reactive dye, which has the following structural general formula:
in the formula, x is more than 0 and less than or equal to 2, y is more than 0 and less than or equal to 2, z is more than 0 and less than or equal to 2, and x + y + z is 3.5-4.
The invention also provides a preparation method of the bright green reactive dye based on the phthalocyanine azo-based double-color body, which comprises the following steps:
(1) adding chlorosulfonic acid into a reaction container at room temperature, adding copper phthalocyanine under stirring at room temperature, performing sulfonation and chlorination reactions, adding thionyl chloride for reaction after the reaction is finished, adding a reaction system into ice water, and performing suction filtration to obtain copper phthalocyanine sulfonyl; wherein the molar ratio of the copper phthalocyanine to the chlorosulfonic acid to the thionyl chloride is 1-2: 40-50: 20-25;
(2) preparing the copper phthalocyanine sulfonyl chloride in the step (1) into a solution, pulping, adding a 2, 4-diaminobenzene sodium sulfonate solution and pyridine for reaction, and adding ammonia water for continuous reaction to obtain a turquoise blue base solution; wherein the molar ratio of the copper phthalocyanine sulfonyl chloride to the 2, 4-diaminobenzene sulfonic acid sodium salt to the ammonia water is 1: 1-2;
(3) preparing cyanuric chloride into a solution, pulping, adding the turquoise blue base solution obtained in the step (2), and stirring for reaction to obtain a condensate; wherein the molar ratio of the turquoise blue group to the cyanuric chloride is 1: 1.02-2.04;
(4) adding 2, 4-diaminobenzene sulfonic acid sodium into the first condensate solution in the step (3), and stirring for reaction to obtain a second condensate; wherein the molar ratio of the condensate to the 2, 4-diaminobenzene sulfonic acid sodium salt is 1: 1-2;
(5) cooling the secondary condensate solution in the step (4) in an ice water bath, adding concentrated hydrochloric acid, dropwise adding a sodium nitrite solution, and keeping the temperature of-5-0 ℃ for continuous reaction for 1.5-2 hours after the dropwise adding is finished to obtain diazonium salt; wherein the molar ratio of the second condensate to the concentrated hydrochloric acid to the sodium nitrite is 1: 2-3: 1-2;
(6) adding a coupling component Rn into the diazonium salt obtained in the step (5) to react; wherein the molar ratio of the diazonium salt to the Rn is 1: 1-2.
The sulfonation temperature in the step (1) is 130-140 ℃, and the sulfonation time is 3-6 h; the chlorination temperature is 90-105 ℃, and the chlorination time is 1-3 h.
The mass fraction of the copper phthalocyanine sulfonyl chloride solution in the step (2) is 10-20%, the pulping temperature is 0-5 ℃, and the time is 50-70 min; the mass fraction of the 2, 4-diaminobenzene sulfonic acid sodium salt solution is 10-20%.
The reaction conditions after adding the 2, 4-diaminobenzene sodium sulfonate in the step (2) are as follows: the pH value is 6.5-7, and the reaction is carried out for 5-7 h under the condition of 10-20 ℃; the reaction conditions after adding ammonia water are as follows: the pH value is 9-10, the temperature is 30-35 ℃, the reaction is carried out for 4-5 h, and then the reaction is carried out for 2-3 h at the pH value of 9-10 and the temperature of 40-50 ℃.
The mass fraction of the cyanuric chloride solution in the step (3) is 10-20%, the pulping temperature is 0-2 ℃, and the pulping time is 20-40 min; pre-cooling the turquoise blue base solution to below 5 ℃, and reducing the pH value to 6; the reaction temperature is 0-10 ℃, the pH value is adjusted to 3-5, and the reaction time is 10-12 h.
The reaction temperature in the step (4) is 35-40 ℃, the pH value is adjusted to 7-8, and the reaction time is 7-9 h.
The coupling component Rn in the step (6) is N-ethyl-3-methylsulfonic acid-4-methyl-6-hydroxy-2-pyridone or 1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-2-pyrazoline-5-ketone.
The coupling reaction temperature in the step (6) is 10-15 ℃, the pH value is 6.5-7, and the reaction time is 6-7 h.
The invention also provides an application of the phthalocyanine azo-based double-color body light green reactive dye, and a dry powder product is prepared by adding a dispersant, a cosolvent, a filler or coupling liquid of other performance improvement aids and performing spray drying treatment.
The phthalocyanine azo-based double-chromophore bright green reactive dye can also contain a part of other dye components and a part of impurities, because the dye inevitably contains a small part of impurities and electrolytic powder (sodium chloride and the like) in the conventional synthesis or salting-out process, and the existence of the substances does not influence the technical effect of the invention.
The invention also provides a reactive dye composition printing dye with high color fixing rate for textile products such as cotton, hemp, regenerated fiber and the like.
Advantageous effects
(1) According to the invention, a phthalocyanine and azo mixed color system is introduced into molecules at the same time, so that the product is bright and tender green, novel in structure and high in molar extinction coefficient;
(2) according to the invention, a phthalocyanine and azo mixed color-developing system is introduced into molecules to synthesize the single-component light green reactive dye, so that the problems of color compatibility, color fastness, great dyeing and finishing processing difficulty and the like of the emerald blue dye and the light yellow dye are solved;
(3) the bright green reactive dye prepared by the invention is used for printing cotton, hemp and regenerated fiber fabrics, has good lifting power and various color fastness, and has good application prospect.
Drawings
FIG. 1 is a chart of the infrared spectrum of the reactive dye of example 1;
FIG. 2 is a chart of the infrared spectrum of the reactive dye of example 2;
FIG. 3 is a graph of the UV-VIS absorption spectrum of the reactive dye of example 3;
FIG. 4 is a graph of the printing lifting force of the reactive dye on cotton fabric in example 4.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
The synthesis process of the double-color body light green reactive dye with the structure as follows:
(1) preparation of copper phthalocyanine sulfonylchloride: under the condition of room temperature, adding 80mL of chlorosulfonic acid into a three-neck flask provided with a reflux condenser tube and a tail gas absorption device, adding 15g of copper phthalocyanine under stirring, heating to 135 ℃ for reaction for 5h, cooling to 60 ℃, adding 22mL of thionyl chloride, heating to 100 ℃ for reaction for 2h, cooling to below 30 ℃, slowly adding the system into ice water under the condition of stirring, carrying out suction filtration, and washing a filter cake with a proper amount of ice water to obtain 58g of copper phthalocyanine sulfonyl chloride filter cake.
(2) Preparation of copper phthalocyanine turquoise blue base: pulping the copper phthalocyanine sulfonyl chloride in the step (1) for 1h under the ice-water bath condition. Accurately weighing 5.04g of 2, 4-diaminobenzene sulfonic acid sodium salt (m-bis) to prepare a 15% solution, adjusting the pH value to 6-6.5, dropwise adding the solution into uniformly pulped copper phthalocyanine sulfonyl chloride, and adding a proper amount of pyridine as a catalyst. Reacting for 7 hours under the conditions that the pH value is 6.5-7 and the temperature is 15-20 ℃, heating to 30-35 ℃, adding 1.03mL of ammonia water for reacting for 5 hours, then heating the pH value to 9-10, heating to 40-45 ℃, reacting for 3 hours, and detecting the reaction end point by utilizing thin layer chromatography.
(3) Preparation of turquoise blue base condensate: weighing 5.11g of cyanuric chloride to prepare a 20% solution, and pulping in ice water at 0-2 ℃ for 30 min. And (3) cooling the turquoise blue base solution obtained in the step (2) to below 5 ℃, reducing the pH value to 6, dropwise adding into cyanuric chloride, reacting at the temperature of 0-10 ℃, at the pH value of 4-5 for 12h, and detecting the reaction end point by using thin-layer chromatography.
(4) Preparation of the second condensate: and (3) adding 5.04g of 2, 4-diaminobenzene sulfonic acid sodium salt dry powder into the primary condensed liquid obtained in the step (3), heating to 35-40 ℃, raising the pH to 7-8, reacting for 7 hours, and detecting the reaction end point by using a thin layer chromatography.
(5) Preparation of diazonium salt: and (3) cooling the secondary condensate obtained in the step (4) to below 5 ℃ in an ice water bath, adding 5.20g of concentrated hydrochloric acid solution with the mass fraction of 36.5%, slowly dripping 1.82g of 30% aqueous solution prepared from sodium nitrite in 1h, and reacting for 1.5h at the temperature of-5-0 ℃.
(6) Coupling reaction: weighing 7.01g of N-ethyl-3-methanesulfonic acid-4-methyl-6-hydroxy-2-pyridone, quickly adding the weighed mixture into the diazonium salt obtained in the step (5), and reacting for 6-7 h at the temperature of 10-15 ℃ and the pH value of 6.5-8 to reach the end point of the coupling reaction. Drying the obtained product at 65 ℃ to obtain a bright green reactive dye with a yield of 63.6%, salting out the dye, and performing DMF-CH2Cl2Recrystallization purification, and its infrared spectrum is shown in FIG. 1.
The dye is 3323.85cm-1The strong broad peak of (A) is a broad peak formed by stretching vibration of N-H and OH; the weak absorption peaks at 2958.72 and 2934.74 are CH3And CH2The stretching vibration absorption peak of (1); 1561.03cm-1The absorption of (a) is C ═ N stretching vibration absorption peak; 1492.29cm-1The absorption of (a) is a characteristic absorption peak of the benzene ring; 1392.24cm-1The absorption of (a) is a C-N telescopic vibration absorption peak on the isoindole ring; 1329.99cm-1The compound has a strong absorption peak, namely a broad peak formed by S ═ O stretching vibration and phthalocyanine ring characteristic absorption; 1155.77, 1088.56cm-1And 1023.17cm-1Characteristic absorption peak of phthalocyanine ring; 741.37cm-1Is the stretching vibration peak of C-S; 907.58cm-1Is a Cu-N vibration absorption peak.
Example 2
The synthesis process of the double-color body bright green reactive dye with the following structure has the preparation method basically the same as that in the embodiment 1, except that the feeding proportion is different:
(1) preparation of copper phthalocyanine sulfonylchloride: under the condition of room temperature, adding 80mL of chlorosulfonic acid into a three-neck flask provided with a reflux condenser tube and a tail gas absorption device, adding 15g of copper phthalocyanine under stirring, heating to 135 ℃ for reaction for 5h, cooling to 60 ℃, adding 22mL of thionyl chloride, heating to 100 ℃ for reaction for 2h, cooling to below 30 ℃, slowly adding the system into ice water under the condition of stirring, carrying out suction filtration, and washing a filter cake with a proper amount of ice water to obtain 58g of copper phthalocyanine sulfonyl chloride filter cake.
(2) Preparation of copper phthalocyanine turquoise blue base: pulping the copper phthalocyanine sulfonyl chloride in the step (1) for 1h under the ice-water bath condition. Accurately weighing 10.08g of 2, 4-diaminobenzene sulfonic acid sodium salt (m-bis) to prepare a 15% solution, adjusting the pH value to 6-6.5, dropwise adding the solution into uniformly pulped copper phthalocyanine sulfonyl chloride, and adding a proper amount of pyridine as a catalyst. Reacting for 5 hours under the conditions that the pH value is 6.5-7 and the temperature is 15-20 ℃, heating to 30-35 ℃ for reacting for 5 hours, then adding 1.03mL of ammonia water, heating to 40-45 ℃, heating the pH value to 9-10, reacting for 6 hours, and detecting the reaction end point by using a thin layer chromatography.
(3) Preparation of a condensate: weighing 10.21g of cyanuric chloride to prepare a 20% solution, and pulping in ice water at 0-2 ℃ for 30 min. And (3) cooling the turquoise blue base solution obtained in the step (2) to below 5 ℃, reducing the pH value to 6, dropwise adding into cyanuric chloride, reacting at 0-10 ℃, for 13h, and detecting the reaction end point by using a thin-layer chromatography, wherein the reaction pH value is 5.
(4) Preparation of the second condensate: and (3) adding 10.08g of 2, 4-diaminobenzene sulfonic acid sodium salt dry powder into the primary condensed liquid in the step (3), heating to 35-40 ℃, raising the pH to 7-8.5, reacting for 7-9 h, and detecting the reaction end point by using a thin layer chromatography.
(5) Preparation of diazonium salt: and (3) cooling the secondary condensate obtained in the step (4) to below 5 ℃ in an ice water bath, adding 10.40g of concentrated hydrochloric acid solution with the mass fraction of 36.5%, slowly dripping 3.64g of sodium nitrite prepared into 30% aqueous solution within 1 hour, and reacting for 1.5 hours at the temperature of-5-0 ℃ after dripping.
(6) Coupling reaction: balanceAnd (3) taking 14.02g of N-ethyl-3-methanesulfonic acid-4-methyl-6-hydroxy-2-pyridone, quickly adding the mixture into the diazonium salt in the step (5), and reacting for 7-8 h at the temperature of 10-15 ℃ and the pH value of 6.5-8 to reach the end point of the coupling reaction. Drying the obtained product at 65 deg.C to obtain bright green reactive dye with yield of 64.7%, salting out the dye, and adding DMF-CH2Cl2Recrystallization purification, and its infrared spectrum is shown in FIG. 2.
The dye is 3400.18cm-1The strong broad peak of (A) is a broad peak formed by stretching vibration of N-H and OH; the weak absorption peaks at 2958.72 and 2934.74 are CH3And CH2The stretching vibration absorption peak of (1); 1618.31cm-1is-CONH-stretching vibration absorption peak; 1566.73cm-1The absorption of (a) is C ═ N stretching vibration absorption peak; 1500.45cm-1The absorption of (a) is a characteristic absorption peak of the benzene ring; 1396.46cm-1The absorption of (a) is a C-N telescopic vibration absorption peak on the isoindole ring; 1329.28cm-1The compound has a strong absorption peak, namely a broad peak formed by S ═ O stretching vibration and phthalocyanine ring characteristic absorption; 1188.59, 1090.01cm-1And 1026.23cm-1Characteristic absorption peak of phthalocyanine ring; 743.51cm-1Is the stretching vibration peak of C-S; 908.35cm-1Is a Cu-N vibration absorption peak.
Example 3
The light green reactive dyes of examples 1 and 2 were prepared to have a concentration of 1.26X 10-5mol/L、0.97×10- 6The ultraviolet-visible absorption spectrum curve of each dye was measured for a mol/L aqueous solution, and the results are shown in fig. 3, and the molar extinction coefficient thereof was calculated, and the results are shown in table 1:
TABLE 1
Example 4
The bright green reactive dyes in the examples 1 and 2 are used for printing cotton fabrics, and bright green color tone can be provided for the fabrics.
5 parts of urea, 1 part of anti-dyeing salt, 2.5 parts of baking soda, 5 parts of sodium alginate and 86.5 parts of warm water are mixed into paste in a container and fully stirred to be uniform, so as to prepare the printing paste. The dyes obtained in examples 1 and 2 were mixed uniformly with 49.5 parts (1%), 1 part (2%), 2 parts (4%), 3 parts (6%) and 4 parts (8%) of the above printing pastes, respectively, to prepare a printing paste, and the paste was printed on a cotton cloth with a 200-mesh printing screen, baked at 80 ℃ for 4min and steamed at 105 ℃ for 8 min. Then washing with a large amount of cold water, soaping, washing with hot water, washing with cold water, and drying. The apparent color depth K/S value of the bright green dye is tested, and as shown in figure 4, the bright green dye is shown to have good promotion performance, the color yield is gradually improved along with the increase of the dye concentration during printing.
Example 5
The printed cotton fabric of example 4 with a dye concentration of 4% was subjected to various color fastness tests, the reference standards for this example being: the rubbing color fastness ISO 105-X12(2001), the washing color fastness ISO 105-C03(2010), the light color fastness ISO105-B02(2013), and the test results are shown in Table 2.
TABLE 2
Claims (3)
1. A light green reactive dye based on phthalocyanine azo-based double color bodies is characterized in that: the structural formula is as follows:
2. a preparation method of a bright green reactive dye based on phthalocyanine azo double-color body comprises the following steps:
(1) preparation of copper phthalocyanine sulfonylchloride: under the condition of room temperature, adding 80mL of chlorosulfonic acid into a three-neck flask provided with a reflux condenser tube and a tail gas absorption device, adding 15g of copper phthalocyanine under stirring, heating to 135 ℃ for reaction for 5 hours, cooling to 60 ℃, adding 22mL of thionyl chloride, heating to 100 ℃ for reaction for 2 hours, cooling to below 30 ℃, slowly adding the system into ice water under the condition of stirring, carrying out suction filtration, and washing a filter cake with a proper amount of ice water to obtain 58g of copper phthalocyanine sulfonyl chloride filter cake;
(2) preparation of copper phthalocyanine turquoise blue base: pulping the copper phthalocyanine sulfonyl chloride in the step (1) for 1h under the condition of ice-water bath; accurately weighing 10.08g of 2, 4-diaminobenzene sulfonic acid sodium salt to prepare 15% solution, adjusting the pH value to 6-6.5, dropwise adding the solution into uniformly pulped copper phthalocyanine sulfonyl chloride, and adding a proper amount of pyridine as a catalyst; reacting for 5 hours under the conditions that the pH value is 6.5-7 and the temperature is 15-20 ℃, heating to 30-35 ℃ for reacting for 5 hours, then adding 1.03mL of ammonia water, heating to 40-45 ℃, heating the pH value to 9-10, reacting for 6 hours, and detecting the reaction end point by using a thin layer chromatography;
(3) preparation of a condensate: weighing 10.21g of cyanuric chloride to prepare a 20% solution, and pulping in ice water at 0-2 ℃ for 30 min; cooling the turquoise blue base solution obtained in the step (2) to below 5 ℃, reducing the pH value to 6, dropwise adding into cyanuric chloride, wherein the reaction temperature is 0-10 ℃, the reaction pH value is 5, the reaction time is 13h, and detecting the reaction end point by using a thin-layer chromatography;
(4) preparation of the second condensate: adding 10.08g of 2, 4-diaminobenzene sulfonic acid sodium salt dry powder into the primary condensed liquid obtained in the step (3), heating to 35-40 ℃, raising the pH to 7-8.5, reacting for 7-9 h, and detecting the reaction end point by using a thin layer chromatography;
(5) preparation of diazonium salt: cooling the secondary condensate obtained in the step (4) to below 5 ℃ in an ice water bath, adding 10.40g of concentrated hydrochloric acid solution with the mass fraction of 36.5%, slowly dripping 3.64g of sodium nitrite into the concentrated hydrochloric acid solution to prepare 30% aqueous solution within 1 hour, and reacting for 1.5 hours at the temperature of-5-0 ℃ after dripping;
(6) coupling reaction: weighing 14.02g of N-ethyl-3-methylsulfonic acid-4-methyl-6-hydroxy-2-pyridone, quickly adding the weighed materials into the diazonium salt obtained in the step (5), and reacting for 7-8 h at the temperature of 10-15 ℃ and the pH value of 6.5-8 to reach the end point of the coupling reaction; and drying the obtained product at the temperature of 65 ℃ to obtain the bright green reactive dye.
3. Use of a bright green reactive dye based on phthalocyanine azo-based dichromate as claimed in claim 1, characterized in that: adding dispersant, cosolvent, filler or other performance improving assistants, and spray drying to obtain dry powder product.
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